Malic acid

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O5
Molecular Weight	134.0874
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H6O5
Molecular Weight	134.0874
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.cosmeticsinfo.org/ingredient/sodium-malate | https://www.food.gov.uk/science/additives/enumberlist#h_7 | https://www.ncbi.nlm.nih.gov/pubmed/11358110 | https://www.ncbi.nlm.nih.gov/pubmed/9477166http://gov.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/FR330.pdf | https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf

Malic acid is a racemic mixture of naturally occuring L-malic acid and D-malic acid. Malic acid is used in cosmetic product formulations and is generally recognized as safe as a direct food additive for use as a flavor enhancer, flavoring agent and adjuvant, and as a pH control agent. In medicine malic acid is also used in the preparation of salts. The racemic malic acid is an active ingredient of Acerbine solution, which is applied for the treatment of superficial skin injuries. L-Malic acid is an intermediate of the Krebs cycle.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cisplatin-induced toxicity 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9477166 https://www.ncbi.nlm.nih.gov/pubmed/9514605	Secondary	Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8974556 https://www.ncbi.nlm.nih.gov/pubmed/1458176	Preventing	Preclinical	Unknown Approved Use Unknown
Skin injuries 8 Sources: https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf	Curative	Approved 8307	ACERBINE Approved Use Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.

PubMed

Title	Date	PubMed
Metabolic regulation of pH in plant cells: role of cytoplasmic pH in defense reaction and secondary metabolism.	2001	11407758
Final report on the safety assessment of Malic Acid and Sodium Malate.	2001	11358110
Development of a new calcium phosphate cement that contains sodium calcium phosphate.	2001 Apr	11246953
Survey of normal appearing mouse strain which lacks malic enzyme and Nad+-linked glycerol phosphate dehydrogenase: normal pancreatic beta cell function, but abnormal metabolite pattern in skeletal muscle.	2001 Apr	11451371
Physiological basis of reduced AL tolerance in ditelosomic lines of Chinese Spring wheat.	2001 Apr	11346958
Inhibiting expression of a tomato ripening-associated membrane protein increases organic acids and reduces sugar levels of fruit.	2001 Apr	11346954
Reevaluating the free-ion activity model of trace metal toxicity toward higher plants: experimental evidence with copper and zinc.	2001 Apr	11345467
Phlebotomine sandflies in Venezuela. V. Review of the genus Brumptomyia (Diptera: Psychodidae), with description of the female of Brumptomyia devenanzii, re-description of the male and isozymatic profile.	2001 Apr	11339889
Carbohydrate deprivation reduces NADPH-production in fish liver but not in adipose tissue.	2001 Aug	11404182
Characterization of a novel complex from halophilic archaebacteria, which displays chaperone-like activities in vitro.	2001 Aug 10	11395490
Alteration of the specificity of malate dehydrogenase by chemical modulation of an active site arginine.	2001 Aug 17	11389140
Substrate and cofactor binding to fluorescently labeled cytoplasmic malate dehydrogenase.	2001 Feb 9	11342039
[Lactate and malate dehydrogenase activity in the sterlet and Russian sturgeon under conditions of the widespread muscular pathology].	2001 Jan-Feb	11424523
Thyroid hormone--sympathetic interaction and adaptive thermogenesis are thyroid hormone receptor isoform--specific.	2001 Jul	11435461
Massive sequence comparisons as a help in annotating genomic sequences.	2001 Jul	11435413
Altered expression and function of mitochondrial beta-oxidation enzymes in juvenile intrauterine-growth-retarded rat skeletal muscle.	2001 Jul	11420423
Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates.	2001 Jul	11322966
Relationships between inhibition constants, inhibitor concentrations for 50% inhibition and types of inhibition: new ways of analysing data.	2001 Jul 1	11415458
pH-dependent investigations of vanadium(V)-peroxo-malate complexes from aqueous solutions. In search of biologically relevant vanadium(V)-peroxo species.	2001 Jul 16	11442368
Transcriptome meets metabolome: hierarchical and metabolic regulation of the glycolytic pathway.	2001 Jul 6	11445079
The effect of nucleotides and mitochondrial chaperonin 10 on the structure and chaperone activity of mitochondrial chaperonin 60.	2001 Jun	11422376
Aluminum speciation studies in biological fluids. Part 7. A quantitative investigation of aluminum(III)-malate complex equilibria and their potential implications for aluminum metabolism and toxicity.	2001 Jun	11410234
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
Energetic determinants of tyrosine phosphorylation of focal adhesion proteins during hypoxia/reoxygenation of kidney proximal tubules.	2001 Jun	11395393
A pre-genetic study of the isoforms of malic enzyme associated with lipid accumulation in Mucor circinelloides.	2001 Jun	11390681
What controls the outer mitochondrial membrane permeability for ADP: facts for and against the role of oncotic pressure.	2001 Jun 1	11334786
Myoadenylate deaminase deficiency does not affect muscle anaplerosis during exhaustive exercise in humans.	2001 Jun 15	11410643
Histochemical study of acute and chronic intraperitoneal nicotine effects on several glycolytic and Krebs cycle dehydrogenase activities in the frontoparietal cortex and subcortical nuclei of the rat brain.	2001 Jun 15	11398187
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.	2001 Jun 29	11434921
The homeodomain proteins PBX and MEIS1 are accessory factors that enhance thyroid hormone regulation of the malic enzyme gene in hepatocytes.	2001 Jun 29	11331288
Non-photosynthetic 'malic enzyme' from maize: a constituvely expressed enzyme that responds to plant defence inducers.	2001 Mar	11352460
Relationship between NADP-specific isocitrate dehydrogenase and glutathione peroxidase in aging rat skeletal muscle.	2001 Mar	11311317
A study into the role of L-aspartic acid on the metabolism of L-malic acid and D-glucose by Oenococcus oeni.	2001 Mar	11298233
[Properties of gluconeogenesis enzymes from flatworms].	2001 Mar-Apr	11452789
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.	2001 May	11440113
New phenolic constituents from the fruit juice of Phyllanthus emblica.	2001 May	11383602
Comprehensive chemical profiling of gramineous plant root exudates using high-resolution NMR and MS.	2001 May	11382236
Cloning and functional characterization of the 5' flanking region of the human mitochondrial malic enzyme gene. Regulatory role of Sp1 and AP-2.	2001 May	11358520
Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex.	2001 May	11351103
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.	2001 May	11351102
Oxyconformity in the intertidal worm Sipunculus nudus: the mitochondrial background and energetic consequences.	2001 May	11337254
Amide hydrogen exchange shows that malate dehydrogenase is a folded monomer at pH 5.	2001 May	11316888
High frequency of cytolytic T lymphocytes directed against a tumor-specific mutated antigen detectable with HLA tetramers in the blood of a lung carcinoma patient with long survival.	2001 May 1	11325844
Determination of organic acids and inorganic anions in wine by isotachophoresis on a planar chip.	2001 May 4	11382288
Enzymatic computing.	2001 May-Jun	11386878
Assimilation of D-malate by Rhodobacter capsulatus E1F1.	2001 Sep	11400062
[Isoenzyme patterns of the isolates of Blastocystis hominis from Guangxi].	2010 Feb	20411749
Method validation and determinations of levofloxacin, metronidazole and sulfamethoxazole in an aqueous pharmaceutical, urine and blood plasma samples using quantitative nuclear magnetic resonance spectrometry.	2012 Jan 15	22265475
The virucidal effect against murine norovirus and feline calicivirus as surrogates for human norovirus by ethanol-based sanitizers.	2013 Aug	23135829
The virucidal effects against murine norovirus and feline calicivirus F4 as surrogates for human norovirus by the different additive concentrations of ethanol-based sanitizers.	2016 Mar	26482918

Patents

Sample Use Guides

In Vivo Use Guide

Oral lethal dose of Sodium Malate in dogs was 1 g/kg

Route of Administration: Oral

In Vitro Use Guide

The effects of two concentrations of disodium malate on the in vitro fermentation of three substrates differing in their forage : concentrate ratio (0.8 : 0.2, 0.5 : 0.5 and 0.2 : 0.8; g/g dry matter; low-, medium- and high-concentrate substrates, respectively) by rumen micro-organisms were studied using batch cultures. Rumen contents were collected from four Merino sheep offered lucerne hay ad libitum and supplemented daily with 400 g concentrate. Disodium malate was added to the incubation bottles to achieve final concentrations of 0, 4 and 8 mmol/l malate and 15N was used as a microbial marker.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:32:53 UTC 2022` Edited by `admin` on `Fri Dec 16 16:32:53 UTC 2022`
Record UNII	817L1N4CKP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Malic acid

Official Name

English

MALIC ACID [USP IMPURITY]

Common Name

English

MALIC ACID, DL-

Common Name

English

POMALOUS ACID

Common Name

English

INS NO.296

Code

English

MALIC ACID [VANDF]

Common Name

English

MALATE

Common Name

English

MALIC ACID [INCI]

Common Name

English

MALIC ACID [USP-RS]

Common Name

English

DL-MALIC ACID

Common Name

English

HYDROXYBUTANEDIOIC ACID, (±)-

Systematic Name

English

MALIC ACID [FCC]

Common Name

English

E-296

Code

English

NSC-25941

Code

English

INS NO. 296

Code

English

E296

Code

English

(±)-MALIC ACID

Common Name

English

MALIC ACID [II]

Common Name

English

MALIC ACID [EP MONOGRAPH]

Common Name

English

HYDROXYBUTANEDIOIC ACID [HSDB]

Common Name

English

INS-296

Code

English

MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]

Common Name

English

D,L-MALIC ACID

Common Name

English

Malic acid [WHO-DD]

Common Name

English

HYDROXYSUCCINIC ACID

Common Name

English

MALIC ACID [MI]

Common Name

English

2-HYDROXYBUTANEDIOIC ACID

Systematic Name

English

MALIC ACID [NF]

Common Name

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-296